Compound ID | 2100

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Streptomycin

Class: Aminoglycoside

Agent Type: Natural product; Small molecule; Direct acting;
Spectrum of activity: Gram-positive, Gram-negative & Antimycobacterial
Mechanism of action: Protein synthesis inhibitor. Binds to the 30S ribosomal subunit
Target Pathogen: Broad spectrum activity including Mycobacterium
Description: Natural product from Streptomyces griseus
Year first mentioned: 1944
Highest development stage: Approved by FDA in 1946
Development status: Approved
Reason dropped: Other formulations were discontinued
Chemical structure(s):
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Molecular weight: 581.57
Iso. SMILES: C[C@H]1[C@@]([C@H]([C@@H](O1)O[C@@H]2[C@H]([C@@H]([C@H]([C@@H]([C@H]2O)O)N=C(N)N)O)N=C(N)N)O[C@H]3[C@H]([C@@H]([C@H]([C@@H](O3)CO)O)O)NC)(C=O)O
InChI Key: UCSJYZPVAKXKNQ-HZYVHMACSA-N
Can. SMILES: C[C@H]1[C@](C=O)([C@H]([C@@H](O1)O[C@@H]2[C@H]([C@@H]([C@H]([C@@H]([C@H]2O)O)N=C(N)N)O)N=C(N)N)O[C@H]3[C@H]([C@@H]([C@H]([C@H](CO)O3)O)O)NC)O
InChI: InChI=1S/C21H39N7O12/c1-5-21(36,4-30)16(40-17-9(26-2)13(34)10(31)6(3-29)38-17)18(37-5)39-15-8(28-20(24)25)11(32)7(27-19(22)23)12(33)14(15)35/h4-18,26,29,31-36H,3H2,1-2H3,(H4,22,23,27)(H4,24,25,28)/t5-,6-,7+,8-,9-,10-,11+,12-,13-,14+,15+,16-,17-,18-,21+/m0/s1
External links:
PubChem link: https://pubchem.ncbi.nlm.nih.gov/compound/19649
Guide to Pharmacology: streptomycin
Citations:
  • https://doi.org/10.1007/s00284-022-03043-9
  • https://doi.org/10.1126/science.102.2637.40
  • https://doi.org/10.1126/science.102.2637.34

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